JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 61 No 3 (2016): Journal of the Chilean Chemical Society
Original Research Papers

A HIGHLY EFFICIENT SYNTHESIS OF SUBSTITUTED IMIDAZOLES VIA A ONE-POT MULTICOMPONENT REACTION BY USING UREA/HYDROGEN PEROXIDE (UHP)

Ali Maleki
Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology
Zahra Alirezvani
Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology
Published September 10, 2016
Keywords
  • Multicomponent reaction,
  • Imidazole,
  • Benzil,
  • Urea,
  • Hydrogen peroxide
How to Cite
Maleki, A., & Alirezvani, Z. (2016). A HIGHLY EFFICIENT SYNTHESIS OF SUBSTITUTED IMIDAZOLES VIA A ONE-POT MULTICOMPONENT REACTION BY USING UREA/HYDROGEN PEROXIDE (UHP). Journal of the Chilean Chemical Society, 61(3). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/90

Abstract

A simple, versatile and highly efficient synthesis of 2,4,5-trisubstituted imidazoles by a condensation reaction of benzil or benzoin, aldehydes and ammonium acetate in the presence of urea/hydrogen peroxide (UHP) as a mild and efficient molecular catalyst in refluxing ethanol is described. The present methodology offers several advantages such as green protocol, inexpensive catalyst, high-to-excellent yields, and simple and easy work-up procedure. 

References

  1. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083, (2012).
  2. M. M. Heravi, M. Daraie, V. Zadsirjan, Mol. Divers. 19, 577, (2015); and the references cited therein.
  3. A. D. Palkowitz, M. I. Steinberg, K. J. Thrasher, J. K. Reel, K. L. Hauser, K. M. Zimmerman, S. A. Wiest, C. A. Whitesitt, R. L. Simon, J. Med. Chem. 37, 4508, (1994).
  4. J. I. Trujillo, J. R. Kiefer, W. Huang, A. Thorarensen, L. Xing, N. L. Caspers, J. E. Day, K. J. Mathis, K. K. Kretzmer, B. A. Reitz, Bioorg. Med. Chem. Lett. 19, 908, (2009).
  5. L. L. Chang, K. L. Sidler, M. A. Cascieri, S. de Laszlo, G. Koch, B. Li, M. MacCoss, N. Mantlo, S. O’Keefe, M. Pang, A. Rolando, W. K. Hagmann, Bioorg. Med. Chem. Lett. 11, 2549, (2011).
  6. D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq, J. Balzarini, Eur. J. Med. Chem. 44, 2347, (2009).
  7. S. Kumar, J. Boehm, J. C. Lee, Nature Rev. Drug Disc. 2, 717, (2003).
  8. A. J. King, D. R. Patrick, R. S. Batorsky, M. L. Ho, H. T. Do, S. Y. Zhang, R. Kumar, D. W. Rusnak, A. K. Takle, D. M. Wilson, Cancer Res. 66, 11100, (2006).
  9. (a) A. Maleki, Tetrahedron 68, 7827, (2012). (b) A. Maleki, Tetrahedron Lett. 54, 2055, (2013). (c) A. Maleki, Helv. Chim. Acta. 97, 587, (2014). (d) A. Maleki, N. Ghamari, M. Kamalzare, RSC Adv. 4, 9416, (2014). (e) A. Maleki, M. Kamalzare, Catal. Commun. 53, 67, (2014). (f) A. Maleki, M. Kamalzare, Tetrahedron Lett. 55, 6931, (2014). (g) A. Maleki, R. Paydar, RSC Adv. 5, 33177, (2015). (h) A. Maleki, Z. Alrezvani, S. Maleki, Catal. Commun. 69, 29, (2015). (i) A. Maleki, H. Movahed, R. Paydar, RSC Adv. 6, 13657, (2016).

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP